CA1179373A - Producing alkylamines from olefins with alkali metal amide catalyst - Google Patents

Producing alkylamines from olefins with alkali metal amide catalyst

Info

Publication number: CA1179373A
Authority: CA; Canada
Prior art keywords: amide; alkali metal; reaction; ammonia; cesium
Prior art date: 1980-12-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000391381A

Other languages

English (en)

French (fr)

Inventor

Guido P. Pez

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Honeywell International Inc

Original Assignee

Allied Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-12-18

Filing date

1981-12-02

Publication date

1984-12-11

1981-12-02 Application filed by Allied Corp filed Critical Allied Corp

1984-12-11 Application granted granted Critical

1984-12-11 Publication of CA1179373A publication Critical patent/CA1179373A/en

Status Expired legal-status Critical Current

Links

229910052783 alkali metal Inorganic materials 0.000 title claims abstract description 32
150000001408 amides Chemical class 0.000 title claims abstract description 31
239000003054 catalyst Substances 0.000 title claims abstract description 30
150000001340 alkali metals Chemical class 0.000 title claims description 9
150000001336 alkenes Chemical class 0.000 title abstract description 19
150000003973 alkyl amines Chemical class 0.000 title abstract description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 93
238000006243 chemical reaction Methods 0.000 claims abstract description 65
-1 ALKALI METAL AMIDE Chemical class 0.000 claims abstract description 34
229910021529 ammonia Inorganic materials 0.000 claims abstract description 34
239000000203 mixture Substances 0.000 claims abstract description 33
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 27
239000005977 Ethylene Substances 0.000 claims abstract description 27
229910052792 caesium Inorganic materials 0.000 claims abstract description 20
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 claims abstract description 17
230000008018 melting Effects 0.000 claims abstract description 17
238000002844 melting Methods 0.000 claims abstract description 17
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims abstract description 15
MTZQAAYXCJMINQ-UHFFFAOYSA-N azanide;rubidium(1+) Chemical class [NH2-].[Rb+] MTZQAAYXCJMINQ-UHFFFAOYSA-N 0.000 claims abstract description 11
238000000034 method Methods 0.000 claims description 38
HOVYSSCJTQTKMV-UHFFFAOYSA-N cesium azanide Chemical compound [NH2-].[Cs+] HOVYSSCJTQTKMV-UHFFFAOYSA-N 0.000 claims description 22
150000005673 monoalkenes Chemical class 0.000 claims description 16
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 15
239000011541 reaction mixture Substances 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 6
230000036647 reaction Effects 0.000 claims 5
239000011734 sodium Substances 0.000 abstract description 15
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 14
229910052700 potassium Inorganic materials 0.000 abstract description 14
239000011591 potassium Substances 0.000 abstract description 14
229910052708 sodium Inorganic materials 0.000 abstract description 14
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 8
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
229940095050 propylene Drugs 0.000 description 8
239000007789 gas Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
230000005496 eutectics Effects 0.000 description 5
239000000376 reactant Substances 0.000 description 5
229910052701 rubidium Inorganic materials 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
230000008014 freezing Effects 0.000 description 4
238000007710 freezing Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000001294 propane Substances 0.000 description 4
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
238000001514 detection method Methods 0.000 description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000004711 α-olefin Substances 0.000 description 3
RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
230000036571 hydration Effects 0.000 description 2
238000006703 hydration reaction Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 2
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910052769 Ytterbium Inorganic materials 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
JENCOQNWECEFQI-UHFFFAOYSA-N azanide;barium(2+) Chemical class [NH2-].[NH2-].[Ba+2] JENCOQNWECEFQI-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
150000005675 cyclic monoalkenes Chemical class 0.000 description 1
RHKZVMUBMXGOLL-UHFFFAOYSA-N cyclopentolate hydrochloride Chemical compound Cl.C1CCCC1(O)C(C(=O)OCCN(C)C)C1=CC=CC=C1 RHKZVMUBMXGOLL-UHFFFAOYSA-N 0.000 description 1
JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000003947 ethylamines Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
239000012035 limiting reagent Substances 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
FEMRXDWBWXQOGV-UHFFFAOYSA-N potassium amide Chemical class [NH2-].[K+] FEMRXDWBWXQOGV-UHFFFAOYSA-N 0.000 description 1
125000006308 propyl amino group Chemical class 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
MBBOMCVGYCRMEA-UHFFFAOYSA-N tryptophol Chemical compound C1=CC=C2C(CCO)=CNC2=C1 MBBOMCVGYCRMEA-UHFFFAOYSA-N 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000391381A 1980-12-18 1981-12-02 Producing alkylamines from olefins with alkali metal amide catalyst Expired CA1179373A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/217,937 US4302603A (en)	1980-12-18	1980-12-18	Producing alkylamines from olefins with alkali metal amide catalyst
US217,937		1980-12-18

Publications (1)

Publication Number	Publication Date
CA1179373A true CA1179373A (en)	1984-12-11

Family

ID=22813084

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000391381A Expired CA1179373A (en)	1980-12-18	1981-12-02	Producing alkylamines from olefins with alkali metal amide catalyst

Country Status (5)

Country	Link
US (1)	US4302603A (de)
EP (1)	EP0054746B1 (de)
JP (1)	JPS57128659A (de)
CA (1)	CA1179373A (de)
DE (1)	DE3168698D1 (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4483757A (en) *	1981-12-23	1984-11-20	Pennwalt Corporation	Photochemical process for preparing amines
US5107027A (en) *	1990-08-01	1992-04-21	Texaco Chemical Company	Tert-butylamine synthesis over montmorillonite clays
US5349109A (en) *	1991-06-04	1994-09-20	The Board Of Regents Of The University Of Oklahoma	Molybdenum-catalyzed amination of olefins
US6576796B1 (en) *	2000-06-28	2003-06-10	Basf Aktiengesellschaft	Process for the preparation of alkylamines
DE10110842A1 (de)	2001-03-07	2002-09-12	Basf Ag	Verfahren zur Herstellung von n-Butylaminen
DE10155524A1 (de) *	2001-11-12	2003-05-22	Basf Ag	Verfahren zur Herstellung von Ethylamin und Butylamin
DE10209528A1 (de) *	2002-03-04	2003-09-18	Basf Ag	Verfahren zur Herstellung von Ethyldimethylamin und Triethylamin
US7157606B2 (en) *	2003-08-13	2007-01-02	Mitsubishi Gas Chemical Company, Inc.	Process for producing an amino composition
EP3441385B1 (de) *	2016-04-06	2020-09-02	Mitsubishi Gas Chemical Company, Inc.	Aminverbindung, aminzusammensetzung und epoxidharzhärter

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2501556A (en) *	1949-12-16	1950-03-21	Du Pont	Alkali metals and their hydrides as catalysts in amine condensation
US2750417A (en) *	1953-04-14	1956-06-12	Ethyl Corp	Amine alkylation
US3439038A (en) *	1965-09-29	1969-04-15	Union Carbide Corp	Process for producing aminoacetylenes from propargylamines
US3412158A (en) *	1965-10-11	1968-11-19	Nat Distillers Chem Corp	Process for the preparation of aliphatic amines
IT1068433B (it) *	1976-10-28	1985-03-21	Snam Progetti	Procedimento per l'lachilazione di ammine secondarie alifatiche

1980
- 1980-12-18 US US06/217,937 patent/US4302603A/en not_active Expired - Fee Related
1981
- 1981-11-16 EP EP81109705A patent/EP0054746B1/de not_active Expired
- 1981-11-16 DE DE8181109705T patent/DE3168698D1/de not_active Expired
- 1981-12-02 CA CA000391381A patent/CA1179373A/en not_active Expired
- 1981-12-17 JP JP56204499A patent/JPS57128659A/ja active Pending

Also Published As

Publication number	Publication date
DE3168698D1 (en)	1985-03-14
EP0054746A1 (de)	1982-06-30
EP0054746B1 (de)	1985-01-30
US4302603A (en)	1981-11-24
JPS57128659A (en)	1982-08-10

Legal Events

Date	Code	Title	Description
2001-12-11	MKEX	Expiry

Publication	Publication Date	Title
US3708539A (en)	1973-01-02	Condensation of ammonia or a primary or secondary amine with an alcohol
US4302603A (en)	1981-11-24	Producing alkylamines from olefins with alkali metal amide catalyst
DK145493B (da)	1982-11-29	Fremgangsmaade til fremstilling af tertiaere aliphatiske aminer
US4410726A (en)	1983-10-18	Vinylation reaction
US4096185A (en)	1978-06-20	Preparation of p-aminobenzotrifluoride
US4336162A (en)	1982-06-22	Alkali metal amide catalyst
US3278575A (en)	1966-10-11	Method for the manufacture of aliphatic nitriles
JPS6121534B2 (de)	1986-05-27
US3446842A (en)	1969-05-27	Production of n,n-dimethylformamide
EP0107441B1 (de)	1986-09-17	Verfahren zur Herstellung von Ameisensäureamiden
JPH04202163A (ja)	1992-07-22	エチレンアミン類の製造法
US4721810A (en)	1988-01-26	Catalytic alkylation of aromatic amines with ethers
US3505403A (en)	1970-04-07	Amidoximes and amidhydrazones and method of preparation
US4334103A (en)	1982-06-08	Process for heterogeneous nucleophilic substitution reactions
US2737447A (en)	1956-03-06	Diborane preparation
CN112004796B (zh)	2023-06-06	N,n-二取代酰胺的制造方法及用于制造n,n-二取代酰胺的催化剂
US4230636A (en)	1980-10-28	Process for producing dimethyl formamide
CA1250595A (en)	1989-02-28	Preparation of amines from olefins using ammonium halide catalysts
JPS5835179A (ja)	1983-03-01	ピペラジンおよびピペラジン誘導体の製造方法
US5574197A (en)	1996-11-12	Method of making a stable non-pyrophoric lithium diorganoamide solution
CA1241968A (en)	1988-09-13	Process for the preparation of aniline derivatives
US20010005764A1 (en)	2001-06-28	Process for the preparation of 2-aminomethyl-1,5-pentanediamine
US3080424A (en)	1963-03-05	Process for preparation of primary and secondary amines
US2938058A (en)	1960-05-24	Arylaminoacenaphthenes as antioxidants for polyalkylene glycol compositions
JPH062716B2 (ja)	1994-01-12	芳香族第二級アミノ化合物の製造方法